Chem. J. Chinese Universities ›› 1981, Vol. 2 ›› Issue (2): 176.

• Articles • Previous Articles     Next Articles

STUDY OF GEOMETRIC ISOMERS OF SOME VINYLPHOSPHATE INSECTICIDES——II——THE STEREOSPECIFIC SYNTHESIS OF THE O,O-DIMETHYL-O-(1-ETHOXYCARBONYL-1-PROPEN-2-YL) PHOSPHATE INSECTICIDE (MIE-YA-JING) AND ITS ANALOGUES

Shao Ruilian, Dong Xiyang, Zhang Chunzao   

  1. Institute of Elemento- Organic Chemistry, Nankai University, Tianjin
  • Received:1980-03-19 Online:1981-04-24 Published:1981-04-24

Abstract: The present report deals with the stereospecific synthesis of the O, O-dimethyl-O-(1-ethoxycarbonyl-1-propen-2-yl) phosphate, an insecticide named Mie-Ya-jing in Chinese. The reaction of phosphorus oxychloride with ethyl acetoacetate in the presence of tributylamine yeilded specifically the E-stereoisomer as the key intermediate, from which E-stereoisomer "Mie-Ya-jing" was prepared by treating with excess of methyl alcohol. It seems that there is a relationship between the steric factors of the base and the E/Zratio obtained. The Z-stereoisomer was synthesized by the action of dimethyl phosphoryl Chloride on ethyl sodioacetoacetate. The other two Mie-Ya-jing derivatives were similarly prepared. The E-isomer proved to be more toxic to insects than the corresponding Z-isomers.

TrendMD: